tert-Butyl isocyanate → 1-Phenyl-3-t-butyl hydantoin

HRID 358091

Reaction equation

HRID 358091 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([N:16]=[C:17]=[O:18])([CH3:15])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH2:8][C:9](=[O:11])[N:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:17]2=[O:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 66025N-Phenylglycine

Product 1

HCID 122633541-Phenyl-3-t-butyl hydantoinYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-phenyl glycine (0.1 mole), t-butyl isocyanate (0.12 mole) and toluene (30 ml) was refluxed for 5 hours and then cooled. The product was collected by filtration and crystallized from ethanol to produce 0.06 mole of the aforedescribed product having a melting point of 116° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturecooled
  3. filtrationThe product was collected by filtration
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-0dbebeb7dd46429c87e48675660834df
Source dataset
uspto-grants-1984_08
Patent number
US04464387

Linked notes

Loading…